Caddi vs Checkbox
Caddi
trycaddi.com
Checkbox
checkbox.aiSide by side
| Figure | Caddi | Checkbox |
|---|---|---|
| Price from | $250/mo | $416.67/mo |
| Free plan | Yes | — |
| Free trial | — | Yes |
| Open source | — | — |
| Web | Yes | Yes |
| API | Yes | Yes |
| Plans published | 5 | 3 |
| Spec score · Legal Conflict Checking Software | 9.2 (#2) | 8.8 (#5) |
| Integrations | The integrations page lists 70+ live connectors and says connectors for public APIs can be built within 24 hours of a request. | Native or documented connections include Gmail/Outlook, Slack, Microsoft Teams, Salesforce, Ironclad and Ivo. |
| Notable news | Product Hunt lists Caddi as launched in 2026 and ranked #2 for the day on its launch listing. | On May 11, 2026 Checkbox announced AI Agent Actions, AI Corrections and Intelligent Status Update capabilities. |
| Purpose | Caddi automates repetitive back-office work across the tools a firm already uses. | Checkbox structures how legal work enters, moves through, and gets resolved for in-house legal teams. |
| Rating on G2 | 0.0 out of 5 from 0 reviews; G2 says there are not enough reviews to provide buying insight. | 4.8 out of 5 from 25 reviews. |
| Security controls | The company states that data is encrypted in transit and at rest and that it performs weekly penetration testing. | Checkbox lists encryption at rest and in transit, patching, antivirus, intrusion detection, penetration testing, vulnerability scanning and administrative logging. |
| Support | The help center offers Getting Started, FAQs, integrations, settings, and product update materials from the Caddi team. | The integrations page says Checkbox’s team can help with best practices and technical support for custom integrations. |
| What it does | Caddi is an AI operations platform that discovers repetitive work, turns narrated screen recordings into automations, and governs agent runs across existing business systems. | Checkbox is an AI legal front door that captures, routes, automates and tracks in-house legal work. |
Plans
Caddi
- IndividualFree
- Startup$250 a month
- Team$250 a month
- Business$6,500 a month
- EnterprisePriced on request
Checkbox
- Starting price$5,000 a year
- CheckboxPriced on request
- Checkbox subscriptionPriced on request
In their own words
Caddi
Caddi automates repetitive back-office work across tools used by legal, financial, and other professional services firms. Discover reads connected systems, ranks recurring work, and presents evidence for its findings. Teams can teach agents a process by screensharing and explaining it, without coding. Govern keeps run history and lets users replay decisions, including the permission applied to each one. Caddi lists more than 70 live connectors, including Clio, DocuSign, Outlook, NetDocuments, Salesforce, QuickBooks, and Microsoft Teams; it says connectors for public APIs can be built within 24 hours of a request. The maker says agents operate within a user’s existing access, process changes need human approval, and users can pause or disconnect a loop mid-queue. Caddi also says it is SOC 2 Type II compliant and does not use connected-system contents to train models. The free Individual plan includes one user, 200 credits, 10 loops per month, and 30 days of run history. Team costs $250 a month per user, billed monthly.
Checkbox
Checkbox organizes how legal requests enter, move through and reach resolution for in-house legal teams. Requests can come from email, Slack, Microsoft Teams, forms and other channels, then AI classifies and routes them. Matter management keeps documents, conversations, tasks, approvals, ownership, status and deadlines together. Legal teams can create no-code workflows for routing requests, assigning tasks and tracking progress. An AI Agent answers routine legal questions from approved policies and directs employees to self-service tools or the appropriate workflow. Listed integrations include Gmail/Outlook, Slack, Microsoft Teams, Salesforce, Ironclad and Ivo. Native connectors, webhooks and REST APIs support custom connections, with API keys or OAuth for standard integrations. Checkbox lists encryption, patching, antivirus scanning, intrusion detection, penetration testing and vulnerability scanning. It states that it completed a SOC 2 Type II examination and is ISO 27001 certified, with ISO 27017 and ISO 27018 compliance. Pricing is provided on request through an Order, and the software is for business use, not consumers.